P-type organic semiconductor material, manufacturing method of same, and display panel

Abstract

A p-type organic semiconductor material, a manufacturing method of the same, and a display panel are provided by the present application. Substitutes are configured to replace hydrogens on ring in a molecular structure of the p-type organic semiconductor material of the present application, therefore a LUMO energy level of the p-type organic semiconductor material obtained is reduced.

1 . A p-type organic semiconductor material having a molecular structure represented by 
       
         
           
           
               
               
           
         
       
       wherein X is a carbon atom or a nitrogen atom, and each of R7, R8, R9, R10, R11, R12 is selected from a first group of substituents;
 when R1 and R2 are not bonded to form a ring, each of R1 and R2 is selected from the first group of substituents; 
 when R1 and R2 are bonded to form the ring, a structure of the ring bonded with R1 and R2 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from a second group of substituents;
 when R3 and R4 are not bonded to form a ring, R3 and R4 are selected from the first group of substituents; 
 when R3 and R4 are bonded to form the ring, a structure of the ring bonded with R3 and R4 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from the second group of substituents;
 when R5 and R6 are not bonded to form a ring, each of R5 and R6 is selected from the first group of substituents; 
 when R5 and R6 are bonded to form the ring, a structure of the ring bonded with R5 and R6 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from the second group of substituents;
 wherein the first group of substituents consists of nitro group, nitrile group, cyano group, halogen group, halogen alkyl group, ester group, silyl group, acyl group, sulfonic group, formyl group, carbonyl group, carboxyl group, sulfoxide group, hydroxyl group, alkoxy group, amino group, aromatic amino group, acylamino group, substituted alkene group, substituted phenyl group, substituted heterocyclic group; and 
 the second group of substituents consists of halogen, CN, 
 
       
         
           
           
               
               
           
         
       
     
     
         2 . The p-type organic semiconductor material of  claim 1 , wherein the p-type organic semiconductor material is one of following compounds: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein each X is independently selected from one of —CN, —F, 
       
       
         
           
           
               
               
           
         
       
     
     
         3 . A manufacturing method of a p-type organic semiconductor material, comprising following steps:
 cyclizing a first reactant containing diketone with a second reactant containing diamine to produce the p-type organic semiconductor material, wherein the p-type organic semiconductor material has a molecular structure represented by   
       
         
           
           
               
               
           
         
       
       wherein X is a carbon atom or a nitrogen atom, and each of R7, R8, R9, R10, R11, R12 is selected from a first group of substituents;
 when R1 and R2 are not bonded to form a ring, each of R1 and R2 is selected from the first group of substituents; 
 when R1 and R2 are bonded to form the ring, a structure of the ring bonded with R1 and R2 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from a second group of substituents;
 when R3 and R4 are not bonded to form a ring, R3 and R4 are selected from the first group of substituents; 
 when R3 and R4 are bonded to form the ring, a structure of the ring bonded with R3 and R4 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from the second group of substituents;
 when R5 and R6 are not bonded to form the ring, each of R5 and R6 is selected from the first group of substituents; 
 when R5 and R6 are c bonded to form the ring, a structure of the ring bonded with R5 and R6 is selected from one of 
 
       
         
           
           
               
               
           
         
       
       and each of m1, m2, m3, and m4 is selected from the second group of substituents;
 wherein the first group of substituents consists of nitro group, nitrile group, cyano group, halogen group, halogen alkyl group, ester group, silyl group, acyl group, sulfonic group, formyl group, carbonyl group, carboxyl group, sulfoxide group, hydroxyl group, alkoxy group, amino group, aromatic amino group, acylamino group, substituted alkene group, substituted phenyl group, substituted heterocyclic group; and 
 the second group of substituents consists of halogen, CN 
 
       
         
           
           
               
               
           
         
       
     
     
         4 . The manufacturing method of the p-type organic semiconductor material of  claim 3 , wherein the first reactant has a molecular structure represented by 
       
         
           
           
               
               
           
         
       
     
     
         5 . The manufacturing method of the p-type organic semiconductor material of  claim 4 , wherein
 when the first reactant is   
       
         
           
           
               
               
           
         
       
       the second reactant comprises 
       
         
           
           
               
               
           
         
         when the first reactant is 
       
       
         
           
           
               
               
           
         
       
       the second reactant comprises 
       
         
           
           
               
               
           
         
       
       and
 when the first reactant is 
 
       
         
           
           
               
               
           
         
       
       the second reactant comprises 
       
         
           
           
               
               
           
         
       
     
     
         6 . The manufacturing method of the p-type organic semiconductor material of  claim 5 , wherein 
       
         
           
           
               
               
           
         
       
       is produced by cyclizing 
       
         
           
           
               
               
           
         
       
       with 
       
         
           
           
               
               
           
         
       
     
     
         7 . The manufacturing method of the p-type organic semiconductor material of  claim 5 , wherein 
       
         
           
           
               
               
           
         
       
       is produced by one or two steps of cyclization reaction of 
       
         
           
           
               
               
           
         
       
     
     
         8 . The manufacturing method of the p-type organic semiconductor material of  claim 3 , wherein the first reactant has a molecular structure represented by 
       
         
           
           
               
               
           
         
       
       and the second reactant has a molecular structure represented by 
       
         
           
           
               
               
           
         
       
     
     
         9 . The manufacturing method of the p-type organic semiconductor material of  claim 8 , wherein the manufacturing method further comprises producing 
       
         
           
           
               
               
           
         
       
       through substitution reaction of 
       
         
           
           
               
               
           
         
       
     
     
         10 . The manufacturing method of the p-type organic semiconductor material of  claim 3 , wherein a molar ratio of the first reactant to the second reactant is 1:1 to 1:10. 
     
     
         11 . The manufacturing method of the p-type organic semiconductor material of  claim 3 , wherein a reaction condition of the step of cyclizing the first reactant containing diketone with the second reactant containing diamine is as below:
 acid catalyst is added under protection of nitrogen, and a reaction temperature is 25° C. to 100° C.   
     
     
         12 . An organic light-emitting diode display panel, comprising a substrate and a plurality of organic light-emitting diode (OLED) devices disposed on the substrate, wherein each of the OLED devices comprises an anode, a cathode, and a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer sequentially stacked between the anode and the cathode, and the hole injection layer comprises the p-type organic semiconductor material of  claim 1 . 
     
     
         13 . The organic light-emitting diode display panel of  claim 10 , wherein the hole injection layer is composed of the p-type organic semiconductor material, and a thickness of the p-type organic semiconductor material is 1 nm to 8 nm. 
     
     
         14 . The organic light-emitting diode display panel of  claim 10 , wherein the hole injection layer is composed of a hole injection material and the p-type organic semiconductor material, and a thickness of the hole injection material accounts for 0.1% to 10% of a thickness of the hole injection layer.